Harlotry: The First Time Someone Paid Me For Sex

Last week, we introduced you to Cate, a writer and former sex worker. This week, she shares the story of her first time with a client.

Despite all my fears and mistakes, my first time as an actual prostitute went very smoothly. While I wasn’t exactly expecting it to be horrific, I also wasn’t expecting the charmingly awkward experience it turned out to be.

I started off with the mistake of riding my bike to the call. It was late June in Chicago and was therefore hot enough that it was nearly impossible to ride a bike for more than a few blocks while remaining fresh as a daisy. By the time I got to my first client’s apartment, I was a sweaty mess. I sat down on the steps of his nice building and tried to fan myself with the book that I’d brought for some reason. Perhaps as a security blanket.

There wasn’t anyone around, but I felt incredibly conspicuous sitting on a tattered messenger bag in front of this nice apartment building in my ripped fishnets, ragged miniskirt, and steel toed boots smoking cigarettes and fanning myself with a copy of whatever Russian novel I was reading at the time. I knew I didn’t look like most people’s idea of a prostitute, but I also knew that it was painfully obvious I didn’t live there. I tried to focus on my imminent work, but that only sent me into a panic: I was about to go upstairs and have sex with a man whose name I had already forgotten but this wasn’t a party, I wasn’t even slightly drunk, it was the middle of the afternoon, and I was going to get paid for it. The very idea was absurd.

When I finally gave up on fanning myself and stood, I was shocked that I was able to walk. My legs felt like Jell-O and I sort of floated into the lobby. Before I punched in the code the guy had emailed me, I tried looking up his name in the directory, hoping that perhaps his first name would be listed. It wasn’t, there was only a last name that was as bland and average as I was sure his first name had been, Chris or Ted or John or something. I decided that I would avoid the subject of a name unless explicitly asked, and dialed the number.

The nameless man instructed me to go to the fourth floor and buzzed me in. The elevator ride up to his floor seemed to take years and I realized I didn’t know which way to turn when I got off the elevator or whether the door would be open. How would I know which door to knock on? What if I knocked on the wrong door? Suddenly my tendency to imagine worst-case scenarios went into overdrive, and by the time I reached the third floor I was certain that I would knock on the wrong door, that a man would answer it, and that I would accidentally have sex (for free!) with one of my actual client’s neighbors. I had decided without a doubt that this was not a good job for me and that I would just cut and run if I didn’t see anyone when I got out of the elevator.

Of course all my fears were unfounded. When I stepped out of the elevator, my first client, this nameless man, was poking his head out of one of the doors that lined the hallway. I came to the door and he led me inside.

It was a cluttered studio apartment with grey wall-to-wall carpeting, a sad-looking beige couch along one wall, and an unmade bed in a corner. There was also a desk with a computer and piles and piles of papers. The computer was softly playing some pop-punk band that was nothing I would ever listen to, and I couldn’t help but wonder whether he had chosen the music to make me feel comfortable. There was a kitchen area that was separated by a half wall from the rest of the room, and its perfect neatness managed to make the rest of the room look more cluttered.

When the nameless man finally closed the door, the first two things I noticed were 1) his absurdly large, round eyes and 2) that he came up to my shoulder. I’d been taller than most of my peers for my entire life and taller than most adults since I was about thirteen, but this was just ridiculous. With the realization that my first client was practically a munchkin, all my nervousness vanished. I suddenly felt very silly for being so frightened. What could possibly go wrong with someone so frankly adorable?

He also wasn’t bad looking, I suppose. While he was a far cry from any of the men I’ve ever been attracted to, I could see how he might one day make some miniature lady quite happy. His non-repulsiveness was a surprise in and of itself. I had assumed that all of my clients would be absolutely disgusting.

I sat down on the couch while the munchkin went to his fridge to get us both mineral waters. I do not like mineral water, but I needed to buy some time when I realized how foolish I was in my choice of footwear: steel-toed boots. While I was the proud owner of many lovely pairs of high-heeled shoes, I had decided that in order to play up the cute rock chick Suicide Girls angle, I should wear my massive, steel-toed combat boots. This would not have been a problem if my boots were older, but unfortunately the trusty Doc Martens I wore throughout much of high school had given out only about six months before and their replacements were still so stiff that they took about five minutes to get off my feet. Ugh.

I began work on one of my boots, but I had significantly underestimated the amount of time it would take the munchkin to return with two cans of La Croix and an envelope. I put the envelope in my bag, opened the mineral water, and pretended to take a sip before returning to the removal of my boots. As determined as I was, my rush to get them both off in record time only led to awkward fumbling and they probably would never have left my feet if the munchkin hadn’t sat on the floor and yanked them off for me. I was terribly embarrassed. I was sure that my inability to remove my boots was a sign of inexperience (it was) and equally certain that that inexperience would be considered negative (of course it wouldn’t).

Once I had my boots off, the munchkin immediately started to kiss me. I had stated in my advertisement that I offered a “girlfriend experience,” but it wasn’t until that moment that I connected the dots. I never had any intention of explicitly forbidding kissing, but I sort of expected it was not something one did with a prostitute. Luckily, there wasn’t enough time for my shock to become apparent because he moved suddenly to the side of my head, sticking his tongue as deep into my ear canal as it would go. I wasn’t sure if slugs burrowed and I was sure they didn’t burrow in people’s ears, but… if they did, I knew what it would feel like.

The only thing I could think to do in order to get his tongue out of my ear was take my shirt off. Unsurprisingly, it worked. Soon he was taking off my bra and slobbering on my nipples, rather than in my ear, giving my a perfect window to pull a condom out of my skirt pocket and suggest we get down to business.

I barely remember the sex; it was all over so fast. I was so focused on my own performance of ecstasy that everything else faded into the background until I realized that the munchkin was finished, and I hadn’t even had time to complete the fake orgasm I had practiced at home in front of the mirror. I’m not sure if it was my lack of pretend pleasure or just the speech he was used to giving after sex, but he immediately launched into the premature ejaculators’ society speech about how he “always comes really fast the first time” but that after some recovery time he can “go all night.” I then politely made it clear that unless he wanted to pay for another hour, I was not going to be putting his claim to the test. So he reached over to put his arms around me.

I hadn’t thought about what would happen after the sex. I already knew that guys liked to talk to their sex workers, but I hadn’t considered that with prostitution, the normal sex worker/client talking would take the place of some strange mimicry of pillow talk. My fleeting shock at this new development didn’t last long: the munchkin was perfectly happy to run the whole conversation. He talked about his ex-girlfriend and how much I reminded him of her, he talked about being vegan, he talked about music, especially Genesis, and he finally settled on Seinfeld and what a masterpiece it was. When I said that I had grown up without a television (true) and had never seen a single episode of Seinfeld (false, I just try to purge them from my memory when I stumble across them) he was aghast. By the time I found a graceful way to interject that I ‘d better be going, he had recapped three of his favorite episodes and I had been there for an extra fifteen minutes.

The fact that I was now officially a whore didn’t really sink in until I was unlocking my bike. It was a lot like losing my virginity, or turning eighteen, in that I didn’t feel any different. I was just acutely aware that I was suddenly somehow different. It had been so easy, so unscary, so very much not like anything I had been led to believe about prostitution.